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Hydrochloric Acid → N-{[4-N-(benzhydryloxycarbonyl)-cytosin-1-yl]-acetyl}-N-[2-(2-nitro-benzenesulfonylamino)-ethyl]-glycine

HRID 1794945
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HRID 1794945 반응식
C([O:3][C:4](=[O:49])[CH2:5][N:6]([C:22](=[O:48])[CH2:23][N:24]1[CH:47]=[CH:46][C:28]([NH:29][C:30]([O:32][CH:33]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])=[N:27][C:25]1=[O:26])[CH2:7][CH2:8][NH:9][S:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20])(=[O:12])=[O:11])C.[OH-].[Li+].Cl.[Cl-].[Na+]>C1COCC1.O>[CH:33]([O:32][C:30]([NH:29][C:28]1[CH:46]=[CH:47][N:24]([CH2:23][C:22]([N:6]([CH2:7][CH2:8][NH:9][S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N+:19]([O-:21])=[O:20])(=[O:11])=[O:12])[CH2:5][C:4]([OH:49])=[O:3])=[O:48])[C:25](=[O:26])[N:27]=1)=[O:31])([C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1
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참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 5234Sodium ChlorideHCID 22222376N-{[4-N-(Benzhydryloxycarbonyl)-cytosin-1-yl]-acetyl}-N-[2-(2-nitro-benzenesulfonylamino)-ethyl]-glycine ethyl ester

생성물 1

HCID 22222393N-{[4-N-(benzhydryloxycarbonyl)-cytosin-1-yl]-acetyl}-N-[2-(2-nitro-benzenesulfonylamino)-ethyl]-glycine수율 78%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of N-{[4-N-(Benzhydryloxycarbonyl)-cytosin-1-yl]-acetyl}-N-[2-(2-nitro-benzenesulfonylamino)-ethyl]-glycine ethyl ester (1.91 g, 2.75 mmol) in THF (10 mL) was added a solution of lithium hydroxide (290 mg, 6.9 mmol) in water (9 mL) at 10° C. After stirring for 1.5 h, the reaction mixture was acidified to pH=3˜4 by adding 1 N HCl solution. The aqueous layer was saturated with sodium chloride and organic layer was separated. The aqueous layer was extracted with THF (15 mL×2). The combined organic layer was dried over sodium sulfate and filtered. The filtrate was concentrated and triturated with ethyl alcohol to precipitate solid. The precipitated solid was filtered off, washed with water, and dried in vacuo to give the tilted product as a white solid (1.42 g, 78%). 1H-NMR (500 MHz; DMSO-d6) δ 8.25˜7.80 (m, 5H), 7.50˜7.25 (m, 10H), 6.94 (d, 0.6H), 6.92 (d, 0.4H), 6.79 (1H, s), 4.78 (s, 1.2H), 4.60 (s, 0.8H), 4.22 (s, 0.8H), 3.94 (s, 1.2H), 3.50 (t, 1.2H), 3.35 (t, 0.8H), 3.24 (q, 1.2H), 3.02 (q, 0.8H).

후처리

  1. customwas separated
  2. extractionThe aqueous layer was extracted with THF (15 mL×2)
  3. dry with materialThe combined organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customtriturated with ethyl alcohol
  7. customto precipitate solid
  8. filtrationThe precipitated solid was filtered off
  9. washwashed with water
  10. customdried in vacuo

출처 및 근거

ORD 기록
ord-fabdec24943d40c3a1d4e6e326d388f3
출처 데이터셋
uspto-grants-2006_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07022851B2

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